Trimethylsilylacetylene → 5-[(Trimethylsilyl)ethynyl]pyrimidine

HRID 2251961Notes

Reaction equation

HRID 2251961 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10]>C(N(CC)CC)C.[Cu]I>[CH3:8][Si:9]([C:12]#[C:13][C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 783445-Bromopyrimidine

Product 1

HCID 153496695-[(Trimethylsilyl)ethynyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8471TriethylamineSolvent

Procedure

Dissolve 5-bromopyrimidine (50.0 g, 314.4 mmol) in triethylamine (400 mL), add copper (I) iodide (1.20 g, 6.2 mmol) and stir mixture under nitrogen. After 15 minutes, add trimethylsilyl acetylene (53.3 mL, 377.3 mmol), followed by dichlorobis(triphenylphosphine) palladium (II) (8.82 g, 12.5 mmol) and stir at room temperature. After 3 hours, filter the solution through Celite®, rinsing with ether. Concentrate the filtrate under reduced pressure. Purification by flash chromatography on silica gel eluting first with hexanes (100%), then with hexanes:ethyl acetate (3:1) gives the title compound: 1H NMR (CDCl3) δ 9.10 (s, 1H), 8.77 (s, 2H), 0.27 (s, 9H).

Workup

  1. stirringstir at room temperature
  2. waitAfter 3 hours
  3. filtrationfilter the solution through Celite®
  4. washrinsing with ether
  5. concentrationConcentrate the filtrate under reduced pressure
  6. customPurification by flash chromatography on silica gel eluting first with hexanes (100%)

Sources & evidence

ORD record
ord-62760f6601cd458286015de7411b8d9d
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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